Bluish-green dyestuffs and color lakes therefrom and process of making same



Patented June 1, 1926.

UNITED STATES, PATENT oFFIcn;

o'r'ro s'rnnnnm, or HooHsr-oN-TfiE-MAIN, GERMANY, AssIGNon, BY MESNE as SIGNMENTS, 'ro GRASSELLI DYESTUFF CORPORATION, on NEW YORK, -N. Y., A

\ CORPORATION OF DELAWARE.

IBLUISE-GREEN DYESTUFFS ANT) COLOR LAKES THEREFROM AND PROCESS OF MAKING SAME.

Io Drawing. Application filed December 18, 1924, Serial No. 756,825, and in Germany December 24, 1928;

versiomof the dyestufi's into color lakes,

however, involves considerable difiiculty in practice due to the fact that the said dye- ,stufi's are very difiicultly soluble. The introduction of additional sulfonic acid groups into the dyestulfs referred to for thepurpose of increasing their solubility has the disadvantage that-the color lakes prepared therefrom are not sufliciently insoluble in water.

Now I have found that by introducing halogen into the naphthalene nucleus the solubility of the dyestuffs in question is con' siderably enhanced, whilst on the other hand the insolubility of the lakes prepared therefrom is not afiected. The dyestuffs may be prepared by treating halogen-1.2 naphthylenediamine sulfonic acids with ferric salts. The dyestufl's thus obtained are superior to the dyestuffs described in U. S. specification No. 1,031,823 not only by their bright and bluer shade but also particularly by their considerably better solubility. Thev are particularly suitable for thepreparation of color-lakes which can be made in the usual manner. The dyestuffs are green powders soluble in water and in concentrated sulfuric- 1. 27 kilos of 8-chloro-1.2-naphthylenediamine-5-sulfonic acid-obtained for instance by coupling 8-chlo-ro-1-naphthylamine-5-sul- I fonic acid with diazobenzene chloride and reducing the resulting azo dyestufl' are dissolved in 500 litres of water and 53 kilos of sodium carbonate "and after having added 136- kilos of sodium acetate the mixture is treated with a solution of 40 kilos of ferric chloride whereupon the dyestufi immediately separates. In a dry state it forms a powder which is readily soluble in water to a greenish-blue solution. Its solution in concentrated sulfuric acid is also bluish-green.

2. A solution of 5 kilos of sulfate of ammonia of 18 per cent in litres of water and a solution of 2 kilos of calcined sodium carbonate in.20 litres of water are mixed with 30 kilos of sulfate of barium. .To this mixture .is added a solution in 100 litres of Water of 3 kilos of the dyestufi (obtainable according to ex'ample'l) from 1.2-naphthylenediamine-S-chloro-5-sulfonic acid and ferr1c chloride,/ and furthermore a solution 'of 9Lkilos' of crystallized barium chloride in litres of water. The resulting color-lake is pressed off and used either in this state as a paste or, after being dried. I claim: 1. Process of producing bluish. green dyestufis which comprises treating a halogenated 1.2-naphthylenediamine sulfonic acid with a soluble ferric salt.

2. Process of producing bluish green dyestufis which comprises treating ahalogenated 1 2-naphthylenedi amine mono-sulfonic 4 acid wlth a soluble ferric salt.

3. Process of producing bluish green dyestufls which comprises treating an 8-halogen- 1.2-n-ap-hthylenediamine sulfonic acid with a soluble ferric salt. p v s 4. Process of producing bluish green dyestufi's which comprises treating an 8-halogen- 1.2-naphthylenediamine mono-sulfonic acid with a soluble ferric salt; v

5. Process of producing a bluish green dyestuif which comprises treating S-halogeri- 1.2-naphthylenediamine-5-sulfonic acid with a soluble ferric salt.

6. As new products, coloring matters substantially identical with those produced by the hereindescribed process which consists essentially in treating halogenated 1.2-naphthylenediamine sulfonic acid with soluble ferric salts, said dyestuii's being green pow ders soluble in Water and in concentrated sulfuric acid 'to green colored solutions but insoluble in most of the organic solvents, and dyeing wool green tints but not dyeing cotton. 4 O

7 As a new product the coloring matter obtainable by treating S chloro-LQ-naphthylenediamine-5-sulfonic acid with soluble ferric salts, being a bluish-green powder, soluble in water, concentrated sulfuric acid and meth l alcohol with the same color, insoluble in ethyl alcohol, acetone, ether, benzene, chloroform and naphtha, dyeing wool bluish-green tints, not dyeing cotton.

8. As new products, color lakes comprising water insoluble salts of dyestuffs substantially identical with those produced by the hereindescribed process which consists essentially in treating halogenated 1.2'2-naphthylenediamine sulfonic acids with soluble ferric salts, said color lakes being green powders of a more bluish tint than the corresponding unhalogenated color lakes.

In testimony whereof, I alfix my signature.

DR. STAEHLIN, OTTO. 

